There are many influential people who are in front of the camera within the fitness industry. Jenn O’Reilly has become one of the most quietly powerful people whose work largely happens behind the scenes, but it plays out in the public domain. Through her work as cultural sports programmer for Palm Heights in Grand Cayman, she was among the first to bring elite athletes into a hospitality setting, setting the formula that has become so popular for today’s health-conscious travelers—and identifying early on that athletes had more to contribute to today’s culture than their sporting talent. Her former roles as head of strategy for Nike and as a retired ex-athlete both inform her vision. Today, she divides her time between New York, London, and Grand Cayman. 

“It can be difficult and confusing for professional athletes to maintain self-worth and a sense of purpose after they have to retire. Sport and training is really hard, but navigating the transition into the real world is very difficult. Athletes are natural perfectionists—even today, training is when I am in my flow state and when I feel my most confident—and a lot of us struggle with the adjustment. It’s very disarming to not be excellent at something; trying new things is a muscle we need to cultivate. I’ve thankfully turned it into an entire career. 

Today, my professional and personal life is all about connection, and training is the relationship that weaves together the two. On behalf of Palm Heights Athletics in Grand Cayman, I work directly with athletes to build cultural programs for sport, where I’ve brought more than 200 professional athletes into the hotel for training and retreats—we’ve had NBA players and Olympic medallists. I also delivered WSA’s training facility in Manhattan. The team at both are visionaries and had the foresight to back how powerful sport and movement could be, well ahead of anyone else. Nothing we do stays in the silo of sport. We always try to unlock sides of an athlete’s personality that they are often unable to express when competing. 

I began my career as a professional cyclist, and today, this really shapes my approach. Protecting the athlete’s performance is the most important thing that I do. It’s the standard on which everything else is built upon, but interestingly, it’s in the background and it’s the thing that no one sees. All my relationships are forged on a deep foundation of trust. It means the coach, the athlete, and the agent, all trust the environment that I create for any activity that we are curating, whether that’s a coffee experience in Grand Cayman with the athlete Jody Williams, or a fashion experience with Becky Downie. It’s really non-negotiable. 

I want to plant a seed in the minds of athletes that, as people, they are really interesting. I’m really motivated to give them a platform before they’ve finished their career, so they have confidence in doing things outside of sport once they retire. 

I grew up in Ireland in a really sporty family. I’m a third-generation international sports person. My grandfather played rugby, my mom was a golfer, and then me; I never actually considered myself sporty because it was what I grew up around. I started my first international career in rowing, and we raced in the one elite race at Royal Henley for women. I also raced for Ireland. I gave it up when I went to university because rowing was so time consuming. 

After a testing day with Cycling Ireland on a Watt Bike, they saw I could put down quite a lot of power. I got a place on the national development team and committed to full-time training for three years in Switzerland at the World Cycling Center. With the Irish team, we did World Cups and World Championships. We didn’t qualify for the London Olympics because of a few medical issues. At that point, I’d already completed my law and tax exam, so I decided to start my career as a tax lawyer. It wasn’t enough for me. I wanted to take my background in business and use that within the world of sport. I packed my bags, gave myself six months, and got a job at a sports marketing agency. That was just the start. 

My career has been a kinetic journey that has fed my passion and my interest—much like training. I love to learn, to expand my thinking around the possibilities, and to consider new ways of experience and new ways to foster connection. When I was at Nike, I did the soccer deals for Liverpool, Chelsea, Tottenham, the FA and the Premier League; I held the strategy and budget for about 700 athletes in the UK. It was an incredible experience, but ultimately, I realized I wanted something more intimate. More hands-on. 

I actually met the team from Palm Heights when I was in a boxing gym in London’s Notting Hill while I was still with Nike. It was very serendipitous. Living the lifestyle means training can unlock job opportunities. Training means that you’re turning up to the same place, usually at the same time, multiple times. It allows you to develop relationships and trust, because everyone is working hard. They told me about Palm Heights and I was really excited about the potential of building something from scratch with them, and shaping it. Training became part of the entire eco-system instead of an add-on. We realized we needed a world-class training facility, and that this would be a selling point. Seven years later, the rest of the world has adopted it. 

For us, authenticity is crucial. We don’t iterate for the sake of iterating; we lean into sports that have a great subculture, like boxing, for example. We don’t just build a boxing facility. We went to Ghana with a group to share and experience the training there, and in tandem, we created a partnership with Ghana Boxing to bring all those athletes to Grand Cayman for their training. Our training spaces are built with the reverence of those experiences and with reverence for the sport. Because of this, athletes know that our equipment is suitable for their training; during their stays, they become part of the fabric at Palm Heights. It’s a very intimate, family atmosphere, and guests always love the fact that elite athletes might be at breakfast. Some of them even do training sessions with our guests. It’s a really rich experience for everyone. 

One of my favourite training moments ever happened at Palm Heights. Stuart McMillan, a seminal speed coach and sprint coach is so revered in his space but he is comfortable being curious. He was curious enough to spend three months at Palm Heights with his athletes, before the Paris Olympics. Palm Heights was filled with all these really interesting people. I personally got a lot from it because I was surrounded daily by people executing at a really high level. I was able to live and breathe it, and join in the weights, and things like that. It was personally fulfilling, but it also unlocked a whole business and we built the success of a program through one partnership. 

Everything that I do is trading on partnerships. It’s about shared values, mutual respect, and always learning. Community is such a buzzword in training today, but it’s really important because in the truest sense of the word, it’s a feeling and an ethos of everyone being of value and being seen. My favorite part of my job is creating environments over a shared passion. Exercise is a great leveller, and I think that no matter your ability, if you are doing the work, you can find common ground with anyone, whether they are an elite athlete or not. Doing hard things brings people together. 

Jennifer O'Reilly founded Protean Sports, a global sport and culture consultancy. Its recent work includes delivering WSA's training centre in Manhattan and building out Palm Heights Athletics in Grand Cayman, where she has curated more than 200 professional athletes, including NBA players and Olympic medallists. A former Head of Strategy at Nike and an international athlete in cycling and rowing, she was appointed a judge for Dubai's Government Excellence Program in 2026 and has spoken on sport and culture internationally, including at Saudi Arabia's first Women's Sport Conference